Formation of (1,2-dihydroxynaphth-4-yl)[tris(diethylamino)]-phosphonium bromides in the reaction of 1,2-naphthoquinones with tris(diethylamino)phosphine

Deoxygenation of Some α-Dicarbonyl Compounds by Tris(diethylamino)phosphine in the Presence of Fullerene C60

“…It should be noted that 1,2-naphthoquinone 6 reacts with aminophosphine 2 to form 2-hydroxy-4-[tris(diethylamino)phosphonium]naphthyl-1-ate. 41 Two fractions were obtained after the separation of the reaction components in the three-component system of aceanthrenequinone 7, hexaethyltriaminophosphine 2, and fullerene C 60 . The first fraction contained unreacted fullerene.…”

“…This compound also behaves unusually in the reaction with aminophosphine 2. 41 Whereas quinone 1 and isatins 3 and 4 give the ketocarbene dimerization products, naphthoquinone 6 undergoes phosphorylation at the four position of the naphthalene fragment. This is likely to be related to the peculiarity of the naphthoquinone's electronic structure which easy turns into the aromatic dihydroxynaphthalene system.…”

“…Attempts to reveal any fullerene products by HPLC failed. It should be noted that 1,2-naphthoquinone 6 reacts with aminophosphine 2 to form 2-hydroxy-4-[tris(diethylamino)phosphonium]naphthyl-1-ate …”

“…1,2-Naphthoquinone 6 , in contrast, does not enter into such a three-component reaction. This compound also behaves unusually in the reaction with aminophosphine 2 . Whereas quinone 1 and isatins 3 and 4 give the ketocarbene dimerization products, naphthoquinone 6 undergoes phosphorylation at the four position of the naphthalene fragment.…”